Where it happened: my bedroom
Langauge: English
Sex: Male
Rating: 6
Category: Straight
I was trying to spy on my 18-year-old sister and her boyfriend afternoons in her bedroom. All I ever succeeded in was the two times I saw each one when they came out of her room to use the bathroom. They were naked and I could see her bush and tits and his cock and balls. Sis could bring him to our house because our parents worked very late in New York City at their law firm and it was her responsibility to take care of me until they got home around 9:30.
Sis was also the captain of the junior-varsity cheerleaders and, since she was both older than the other girls and open about the fact that she was fucking, a couple of the younger girls asked her to advise them about sex. One afternoon when one of her teammates was over I was in my bedroom ignoring them, doing homework when Sis knocked on the door. “I know you’ve been interested in what Bob and I are doing,” she said, “but you’re too young. You could get started if you’ll model for my friend.” She explained that I would come to her room and get naked so she could show off the various parts of my male anatomy and generally let the girl learn about boys from with me.
I was curious enough to agree, so we went to her room and she introduced me to Anne. Sis had me strip and stand there while she lead Anne in examining me. I was nervous and shaking but I loved the attention. Sis calmed me down by praising my body and saying how, “someday soon,” I’d be able to satisfy a woman. Then she had me to lay on the bed and told Anne to touch my 4-inch cock, kiss it, and take it in her mouth and suck. She had Anne play with my balls, sniff my asshole, and kiss me all over. Anne also kissed me all over my crotch. I loved it. After Anne left, Sis explained that Anne had decided to start having sex with her boyfriend but didn’t really know much about a boy’s anatomy. She said I was a very good male model.
Sis had me model for two other girls on her squad after that, but I got tired on the one-way thrill and demanded to be able to touch them. Sis said that wasn’t what she had in mind “and besides, you’re not ready.” So the sessions ended.
That fall Sis went away to college and my parents had a dilemma. They had to work in the city but there was this 12-year-old boy who needed supervision. Mom first tried having me stay with neighbors, but they had kids of their own and it didn’t work out. Then she tried a couple of housekeepers, women who cleaned the house and did the laundry as well as made my dinner. These didn’t work out either because they couldn’t make me do my homework.
Finally, after almost a year, mom found a high-school junior who would meet me when I came home, see that I did my homework, cook me dinner, and stay until 8.
It was Anne.
Over that summer I had begun to mature. I had a small amount of fluffy public hair, my cock was now 4½ inches long (4¾ inches if I cheated measuring), and I was capable of sustaining an erection. I was beating off to some porno my dad thought he’d hidden in his closet.
For the first 2 days Anne and I didn’t acknowledge we knew each other. We settled into a routine where I got home first and Anne would arrive maybe 15 minutes later. We would talk, then I would go to my room for an hour and do my homework. Anne would check it and we would have dinner. Then I could watch TV or play videos until 9 when I had to go to bed.
Day three, when I got home, Anne was already there. So was a guy and I interrupted them as they were making out on the couch. They jumped up and Anne said he was a friend who had brought some school stuff over. She was blushing and the guy left real fast. I got a hard on but went to my room to do my homework and brought it back to Anne as though nothing had happened. She said “I hope you won’t say anything to your mom.” I said I wouldn’t and asked her if she remembered me.
“Oh yes, you had the cutest little penis and I loved having it in my mouth for the first time. Your hairless body really turned me on. Now I see you’ve started to grow up.” With that she reached over and kissed me on the lips. I responded and she giggled. “I’ll show you what your sister wouldn’t,” she said, and gave me a lesson in kissing. After two hours of this she stopped and she made us a quick dinner and I went to bed.
I flew home the next day and couldn’t wait for Anne to arrive. When she did I told her my homework was done (true) and that I wanted some more kissing. “I knew you would be, and I can’t wait!” She brought me over to the couch and laid me down and snuggled up to me. “Touch my breasts,” she said, and I did.
She undid my pants and slipped her hand into my jockeys. My erection got harder and she stroked it. I unbuttoned her blouse and slid one of her breasts out of her bra and sucked it. “Let’s go up to your room,” Anne said.
In my room she undressed me and took her own clothes off. Anne had long brown hair, small breasts, an athletic build, and a lush bush. She did a walk-around me and said “your cock is bigger than it was before.” We lay down on my bed and she rolled me on top of her. She wrapped her legs around me and I felt my cock tight against her bush. Her hands were all over me as we kissed and humped. She taught me how to follow her rhythm.
Anne then slid me off her and laid me on my back. She went down on my cock and began to play with it. In and out of her mouth, then her hands, one cupping my balls and the other stroking my cock. The sensation was like nothing I’d given myself, and I came in her mouth. “Young cum, I love it,” she said.
Anne then rolled onto her back and had me kiss her from her forehead all the way down. I skipped her bush out of embarrassment. When I looked up from her toes I saw she was fingering herself and moaning slightly. “You do it now,” she commanded, so I put my finger into her pussy. “In and out,” she said, and showed me how she liked it, stopping at her clit and tasting her sweetness.
As my erection returned, she felt it against her leg. She told me to stop fingering her and sat up beside me with a dreamy look, then said, “you’re too small for a regular fuck. We’ll do it doggie.” She positioned me behind her, lowered her ass so I had the shortest distance to getting my cock inside her, then guided me in. “Do it slowly, in and out, that’s nice,” she said. It wasn’t long before I came, a violent spasm of cum if not much volume. I was exhausted and slumped against her cheeks.
We fucked once a week throughout the next school year. I agreed that she could have her have her boyfriend over once a week and to stay out of the way. I had a real growth spurt and by the time she graduated I was 3 inches taller, 10 pounds heavier, had more public hair, and my cock was long enough to make the missionary position pleasurable for us both.
And my grades were excellent.
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